1,3-Dioxane-Linked Bacterial Topoisomerase Inhibitors with Enhanced Antibacterial Activity and Reduced hERG Inhibition

ACS Infect Dis. 2019 Jul 12;5(7):1115-1128. doi: 10.1021/acsinfecdis.8b00375. Epub 2019 May 9.

Abstract

The development of new therapies to treat methicillin-resistant Staphylococcus aureus (MRSA) is needed to counteract the significant threat that MRSA presents to human health. Novel inhibitors of DNA gyrase and topoisomerase IV (TopoIV) constitute one highly promising approach, but continued optimization is required to realize the full potential of this class of antibiotics. Herein, we report further studies on a series of dioxane-linked derivatives, demonstrating improved antistaphylococcal activity and reduced hERG inhibition. A subseries of analogues also possesses enhanced inhibition of the secondary target, TopoIV.

Keywords: gyrase; methicillin-resistant; novel bacterial-topoisomerase inhibitors.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Bacterial Agents / chemical synthesis*
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / pharmacology
  • Binding Sites
  • DNA Gyrase / chemistry
  • DNA Gyrase / metabolism*
  • DNA Topoisomerase IV / antagonists & inhibitors
  • DNA Topoisomerase IV / chemistry
  • DNA Topoisomerase IV / metabolism
  • Dioxanes / chemistry*
  • Down-Regulation
  • ERG1 Potassium Channel / metabolism
  • Humans
  • K562 Cells
  • Methicillin-Resistant Staphylococcus aureus / drug effects
  • Methicillin-Resistant Staphylococcus aureus / enzymology*
  • Microbial Sensitivity Tests
  • Models, Molecular
  • Molecular Structure
  • Protein Binding
  • Structure-Activity Relationship
  • Topoisomerase Inhibitors / chemical synthesis*
  • Topoisomerase Inhibitors / chemistry
  • Topoisomerase Inhibitors / pharmacology

Substances

  • Anti-Bacterial Agents
  • Dioxanes
  • ERG1 Potassium Channel
  • KCNH2 protein, human
  • Topoisomerase Inhibitors
  • DNA Topoisomerase IV
  • DNA Gyrase